This Shark Tank billionaire investor started first business at 24 and didn’t take a vacation for 7 years, for one inspiring reason

In a world increasingly drawn to the idea of “work-life balance,” one man chose an unrelenting, all-in path—and it paid off in billions. Long before he became a household name on Shark Tank or owned an NBA franchise, he was just another 24-year-old with no money, no job, and a singular obsession: to build something of his own.

That man was Mark Cuban. In an interview for The Playbook, a video series by Sports Illustrated and Entrepreneur, published on June 3, Cuban reflected on the early years of his career. “I didn’t take a vacation for the next seven years,” he said. “All I did was learn, learn, learn.” Fired from a computer software store and living in a cramped three-bedroom apartment with six roommates, Cuban launched his first company—MicroSolutions—with nothing but grit and an appetite for risk.

No Time Off, No Regrets

Looking back, Cuban doesn’t believe he could’ve achieved his level of success with a more balanced lifestyle. “There is no balance,” he stated plainly. “If you want to work 9-to-5, you can have balance. If you want to crush the game, whatever game you’re in, there’s somebody working 24 hours a day to kick your ass.”


By 32, his first venture sold to CompuServe for $6 million. His next big leap, Broadcast.com, was acquired by Yahoo in 1999 for a whopping $6 billion—setting the foundation for what would become an empire. Today, Cuban has an estimated net worth of $5.7 billion, according to Forbes.

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Rewriting the Rules of Success

But success for Cuban was never just about the money. After becoming a millionaire, he famously threw away his watch. As he shared during a SXSW panel in March 2024, the act was symbolic of reclaiming his time. “I wanted to make enough money so I didn’t have to respond to anybody else,” he said. “I could make my own schedule and live my own life the way I wanted to do it.”

In a February 2024 MasterClass, Cuban reiterated what he sees as the ultimate advantage: effort. “The one thing in life you can control is your effort,” he noted. “And being willing to do so is a huge competitive advantage, because most people don’t.”